(R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: (R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 556031-71-1
• Molecular Formula: C₄₈H₇₉NO₁₃P₂
• Molecular Weight: 940.102
• Mol file: 556031-71-1.mol

Synonyms:(R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property of (R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

There total 9 articles about (R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

n-butyl N-acetyl-β-glucosaminide (94536-61-5) → (R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester (556031-71-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / TsOH / dimethylformamide

2: 80 percent / N₂H₄ / ethanol / 130 °C

3: DCC; 4-pyrrolidino-pyridine / CH₂Cl₂

4: aq. AcOH

With 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; hydrazine; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20021115)41:22<4289::AID-ANIE4289>3.0.CO;2-4

Reference yield:

n-butyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside (155197-37-8) → (R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester (556031-71-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / NaOMe / methanol

2: 82 percent / TsOH / dimethylformamide

3: 80 percent / N₂H₄ / ethanol / 130 °C

4: DCC; 4-pyrrolidino-pyridine / CH₂Cl₂

5: aq. AcOH

With sodium methylate; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; hydrazine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20021115)41:22<4289::AID-ANIE4289>3.0.CO;2-4

Reference yield:

(R)-3-hydroxyoctanoic acid t-butyl ester (176722-11-5) → (R)-3-(Benzyloxy-butyl-phosphinoyloxy)-octanoic acid (2R,3R,4R,5S,6R)-3-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester (556031-71-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / 4H-tetrazole

2: 87 percent / TFA / CH₂Cl₂

3: DCC; 4-pyrrolidino-pyridine / CH₂Cl₂

4: aq. AcOH

With 1H-tetrazole; 4-pyrrolidin-1-ylpyridine; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1002/1521-3773(20021115)41:22<4289::AID-ANIE4289>3.0.CO;2-4

upstream raw materials:

n-butyl N-acetyl-β-glucosaminide

n-butyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside

(R)-3-hydroxyoctanoic acid t-butyl ester

benzyl alcohol

Downstream raw materials:

Bicyclohexyl-4,4'-dicarboxylic acid 4'-benzyl ester 4-{(2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl} ester

4-(3-Benzyloxycarbonyl-propyl)-benzoic acid (2R,3S,4R,5R,6R)-5-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoylamino]-4-[(R)-3-(benzyloxy-butyl-phosphinoyloxy)-octanoyloxy]-6-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester